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A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

This sub-series focuses on photographs of the Day Boys in Hodge Wing in the 1950s and 1960s.

This sub-series focuses on photographs of the Junior Boarding boys of Sargants House. The collection is complete from 1966 to 2010, missing only the years 1970 and 2009.

This sub-series focuses on photographs of the Day Girls in Gunthorpe since its inception in 1997 and contains all but one photographs of the Housemastership of Mary Grimley, only missing the year 2006-2007. It contains both formal and informal photographs as well as some photographs of the Sixth Form girls.

This sub-series contains photographs of the boys in Deanscroft. It covers the whole history of the boarding since its inception in 1948, up to 1988 when the boys were transfered to the new Haywoods house.

The items in this collection are related to Tutoring at Oakham School, either guidelines to staff or resources to use in tutorial with the pupils.

This sub-series is made of various informal photographs of the boys in Deanscroft, especially in the 1960s. It also contains items related to the 50 years Anniversary celebration of Deanscroft & Haywoods House, including a tie designed for the special occasion.

This sub-series focuses on informal photographs of the girls and staff of Gunthorpe House.